A Full Rundown on Hailee Steinfeld and Josh Allen’s Relationship Timeline Now That She’s Pregnant
It looks like Taylor Swift isn’t the only star who caught feelings on the football field! After two years of dating, actor and singer Hailee Steinfeld tied the knot with Buffalo Bills quarterback Josh Allen—and they’re now expecting their first child together.
The duo was first spotted out in New York City fresh off rumors that Josh had split up with his longtime girlfriend, Brittany Williams, in May 2023. Since then, Hailee and Josh have kept their ’ship pretty low-key with the occasional date night and joint public appearance, and with a baby in the near future (!!), it’s likely fans will get to see a lot more of them. But before we look to the future, here’s everything you need to know about Hailee Steinfeld and Josh Allen’s relationship timeline to date.
May 2023
Hailee and Josh are first spotted together during a night out in NYC on May 25. Per pics obtained by the New York Post, they hop out of a black SUV and Josh wraps his arm around the Dickinson actor. This marks Josh’s first outing after rumors that he split with his ex, Brittany Williams, started circulating.
The day after they’re first photographed in NYC, Josh and Hailee head out for a sushi date with friends and explored the city over Memorial Day weekend, according to reports by Us Weekly.
An anonymous source close to Hailee also confirms her relationship with the athlete to People, saying that the “cute couple” had been “hanging out for a few weeks.”
“It’s new, but they are having fun,” the source adds.
June 2023
It’s June, which means it’s still ~early days~ for Hailee and Josh, who “are still dating and getting to know each other,” according to a report by People. “He’s going to be very busy with training camp, though, so they’re not putting too much pressure on things and will see where it goes,” an anonymous source tells the publication.
Another insider dishes to Us Weekly that while they’re only a month into their ’ship, “it’s going really great.” They add that when Hailee and Josh are together, they “laugh a ton” and are “always smiling.”
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“Josh is the first guy in a while she’s been really interested in,” the insider reveals.
August 2023
Josh seemingly addresses his private relationship with Hailee during an appearance on the Pardon My Take podcast. 👀
The Bills QB breaks down stories about him “making out” with the actor and singer, saying, “The fact that anybody cares about that still blows my mind.”
He also opens up about the moment he realized people were snapping pics of him and Hailee on a boat. “I just, like, felt this gross feeling,” he confesses. “Insecurity. No privacy. [I was] like, ‘What is wrong with people?’”
October 2023
After a quiet month, Hailee is spotted shopping in East Aurora, New York, with Josh’s mom at Leveled Up Buffalo. The pair picks up some Bills merch and poses for a pic with the shop’s owner, Lindsey Vega. “Pinch Me,” she captions the post.
A few days later on October 8, Hailee is spotted supporting her beau at a Buffalo Bills vs. Jacksonville Jaguars game in London. She’s caught on the jumbotron next to one of Josh’s good friends, race car driver Daniel Ricciardo. In the name of ~investigative journalism~, ESPN’s Buffalo Bills reporter Alaina Getzenberg snaps a pic of the moment and posts it on Twitter.
Then, on October 12, Hailee and Josh attend a Buffalo Sabres vs. New York Rangers hockey game at KeyBank Center in Buffalo, per People.
January 2024
Hailee is asked about ongoing engagement rumors during an interview at the 2024 Golden Globes after being questioned about a ring on her finger. “I got a cute little doe happening,” she replies as she shows off the deer-shaped diamond 💍 on her right hand.
“No other particular reason other than I thought it was cute,” she adds.
During the convo, the actor is also asked just what all the hype is about when it comes to athletic men (to which we say….everything?!?). “Listen, what isn’t it about? Come on now!” Hailee cheekily replies with a giant smile. Truly, no notes!!!
February 2024
During an appearance on sportscaster Kay Adams’ show, Up & Adams, Josh is asked if he’ll be wearing Enchanté at the Oscars. ICYMI, Enchanté is his friend’s clothing line—which he’s worn at games before!—and Hailee’s movie, Spiderman: Across the Spider-Verse, is up for Best Animated Feature at this year’s Oscars.
“I may,” Josh coyly replies, with a smile on his face.
Meanwhile, a source tells People that Hailee and Josh have a “serious relationship,” adding, “They always planned to spend more time together after his season ended. Things have been going really well. They’re both very family-oriented and driven, and they want to protect their relationship and keep it private. They’ve been on the same page with all of that. Hailee’s in a great place and would love to settle down if it’s with the right guy.”
March 2024
These two make us deeply envious by going to a string of events during Paris Fashion Week. However, one thing we’re not envious of? The fact that Josh apparently had a wardrobe malfunction during one of his date nights with Hailee.
Following vids of the footballer rushing into his and the actor’s hotel (and leaving her behind in the process) making the rounds on TikTok, Josh writes the following explanation on X: “My pants ripped at dinner 🙁🤣 Didn’t want cheeks out…I love Paris 😁.”
The fact that the athlete had a jacket/shirt tied around his waist also checked out with his version of events. Honestly though? Gotta love how much of a sense of humor he has about the whole sitch!
June 2024
Per pics obtained by DeuxMoi, the couple attend a wedding in Cabo in June 2024. According to the outlet, Josh’s former teammate, Kyle Allen, married Summer Juraszek—and Josh’s ex Brittany Williams reportedly attended the ceremony, too. Josh and Hailee sport more casual looks poolside before dressing up in a beige suit and baby blue satin backless dress. Could not be more obsessed with these two!
July 2024
After keeping things low-key for most of their relationship, Josh hard launches Hailee on his Instagram feed with a sweet pic of them during a trip to Paris.
August 2024
During another appearance on Kay Adams’ Up & Adams show on August 2, she greets the Buffalo Bills QB by saying, “Well, well, well…if it isn’t Mr. Hard Launch.”
Josh keeps things quiet as he answers, “We love love.”
October 2024
The duo attends the annual Shakir Family Pet Adoption event hosted by Josh’s Bills teammate Khalil Shakir. A moment of silence for Josh with a puppy (and Hailee right behind him!):
Later in the month, the couple celebrates Halloween together in matching ringleader costumes. Hailee hard launches Josh on her Insta feed as she posts a photo of them kissing in their costumes. S’cute.
November 2024
In the latest issue of her newsletter Beau Society, Hailee opens up about her holiday plans with Josh. Fans theorize that she wrote the issue from his house in New York as she writes, “I take the flurries as a sign that the holidays are quickly approaching.”
She continues, “It can be tricky to get everyone together in one room. Sometimes organizing around people’s travel schedules means Christmas with certain family members happens around Thanksgiving time, and that’s okay! I think of my family traditions as ever-evolving.”
On November 22, the couple announces that they are officially engaged with a joint post on Instagram. In the pic, Josh is seen getting down on one knee, surrounded by a stunning beach sunset and floral arrangement with surrounding candles.
December 2024
Two weeks after announcing the engagement, Josh opens up about the proposal in a Q&A published in the December 5 edition of Hailee’s Beau Society newsletter. “I was very nervous. I think I was most nervous about you finding out about the proposal,” he reveals, per Us Weekly. “It was hard to keep secrets from you and have other people in your life keep secrets from you. Then, multiple times throughout the day a song would come on and I would tear up thinking about how special our day was going to be.”
It probably didn’t help that Hailee apparently woke up that morning with marriage on her mind. “We woke up and were getting ready for brunch and you jumped on the bed and said, ‘Can we get married already?!? What are you waiting for??!'” he recalls. “I replied, ‘Just give me a little more time.'”
Spoiler alert: He managed to keep the proposal a secret until sunset. “You were extremely surprised, you said yes, and that was all that mattered to me. And the sun was out,” Josh adds. As for what he said during the proposal, the NFL athlete reveals he told Hailee that he “couldn’t wait any longer” to be engaged. “I said, ‘I can’t wait to start a family with you.’ I said your full name, and I asked you very nicely. I said please.” Sounds like a true gentleman!
Now that they’re officially engaged, Josh says, “It feels unbelievable to be engaged to someone who is so special and loving and caring and gorgeous and fun and happy.”
Elsewhere in the newsletter, Hailee tells her fans that, while she is overjoyed to share the happy news, there are some details she wants to keep to herself. “While I can’t wait to tell you more about the day and things we’re planning, I’m not ready quite yet. I have to hold this close for a little while longer,” she writes.
January 2025
Hailee is fully in her WAG era! During the January 12 playoff game when the Buffalo Bills took on the Denver Broncos, fans got a sneak peek at Hailee’s game day lewk, thanks to the IG Story of fellow Bills WAG Haillee Watson. In it, you can see Hailee rocking a custom Josh Allen jacket—complete with a No. 17—and a Bills cap.
@hallieewatson/Instagram
A few weeks later, after the Bills lose the AFC Championship game to the Kansas City Chiefs, Hailee still proves herself to be a supportive fiancée during an interview with E! News.
“To say the least, I am so proud of that man,” she gushes. “Everything he’s done and everything that the team has done together, he is the hardest working person I know.”
February 2025
Josh and Hailee finally go red carpet official, showing up at the NFL Honors in New Orleans ahead of the Super Bowl.
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They even kiss when Josh wins an award!
Hailee then graces the cover of Who What Wear, where she opens up about her low-key romance with Josh. She admits that she didn’t see his proposal coming, saying, “You talk to your girlfriends about that, right, where you’re like, ‘I just don’t want to know.'”
She continues, “I’m so grateful that he did it the way he did so that I looked good, and we have these photos that we’ll have and cherish for the rest of our lives that I’m not looking at being like, ‘What was I wearing?’
“We were in Malibu, which is my happy place, and it was magical. That’s the word,” she adds. As for the private nature of their relationship, she explains, “When you realize that so much is already out there in every other aspect of your life, you really learn to cherish the little that isn’t. It just makes things extra special, and it’s just for you.”
May 2025
Hailee and Josh get married in a private ceremony in Southern California on Saturday, May 31, and photos obtained by People show Hailee walking down the aisle in a strapless white gown. And it looks like Larry David—yes, the Larry David—was present at the ceremony.
The Sinners star shares more details in her Beau Society newsletter, writing, “We had the amazing [wedding photographer] Jose Villa and his team with us from Thursday through Sunday to capture all the love. We had a no-phone wedding — we wanted everyone to come and be present. Looking back, it was one of the best decisions we made. But that meant Jose had his work cut out for him, capturing all the magic for us.”
June 2025
Two weeks after their nuptials, the couple go on their honeymoon at a tropical destination. Josh shares a stack of Polaroid pictures in an Instagram post, writing, “Wifey ❤️.”
August 2025
The Buffalo Bills QB gushes about his wedding during the first episode of HBO’s Hard Knocks, saying, “Yeah, that was the best night of my life honestly. And my wife’s life I think. That’s what she says.”
December 2025
Aaaand they’re expecting! On December 12, Hailee takes to IG to show off her growing belly:
So sweet!!!
Aaaand that’s everything we know up ’til now! Check back here to catch more updates on Hailee and Josh’s adorable romance.
